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533-73-3

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533-73-3 Usage

Description

1,2,4-Benzenetriol, also known as hydroxyhydroquinone, is a gray powder that serves as an intermediary metabolite of benzene. It is found in roasted coffee beans and is known for its mutagenic properties, as it can cause the cleaving of DNA single strands through the generation of reactive oxygen species.

Uses

Used in Organic Synthesis:
1,2,4-Benzenetriol is used as an important raw material and intermediate for various applications in the field of organic synthesis. Its unique chemical structure allows for the creation of a wide range of compounds, making it a valuable asset in the development of new materials and products.
Used in Pharmaceuticals:
In the pharmaceutical industry, 1,2,4-Benzenetriol is utilized as a key component in the development of various drugs. Its chemical properties make it suitable for use in the synthesis of medicinal compounds, contributing to the advancement of pharmaceutical research and drug development.
Used in Agrochemicals:
1,2,4-Benzenetriol is also employed in the agrochemical sector, where it is used as a vital intermediate in the production of various agrochemical products. Its role in this industry is crucial for the development of effective and environmentally friendly solutions for agricultural applications.
Used in Dyestuff:
In the dyestuff industry, 1,2,4-Benzenetriol is used as a crucial intermediate for the synthesis of different types of dyes. Its unique chemical properties enable the creation of a wide array of colorants, making it an essential component in the production of various dyestuff products.
Used as a Metabolite of Benzene:
1,2,4-Benzenetriol is recognized as a metabolite of benzene, which is a significant aspect of its applications. This characteristic allows it to be used in various research and industrial processes, particularly in the study of benzene's effects on the environment and human health.

Safety Profile

Poison by subcutaneous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise the triol from Et2O or Et2O/EtOH, and dry it in a vacuum. The picrate forms orange-red needles m 96o. [Beilstein 6 H 1087, 6 I 541, 6 II 1071, 6 III 6276.]

Check Digit Verification of cas no

The CAS Registry Mumber 533-73-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 533-73:
(5*5)+(4*3)+(3*3)+(2*7)+(1*3)=63
63 % 10 = 3
So 533-73-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H

533-73-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A13069)  1,2,4-Trihydroxybenzene, 97%   

  • 533-73-3

  • 1g

  • 314.0CNY

  • Detail
  • Alfa Aesar

  • (A13069)  1,2,4-Trihydroxybenzene, 97%   

  • 533-73-3

  • 5g

  • 1254.0CNY

  • Detail
  • Alfa Aesar

  • (A13069)  1,2,4-Trihydroxybenzene, 97%   

  • 533-73-3

  • 25g

  • 5240.0CNY

  • Detail
  • Aldrich

  • (173401)  1,2,4-Benzenetriol  ReagentPlus®, 99%

  • 533-73-3

  • 173401-1G

  • 762.84CNY

  • Detail
  • Aldrich

  • (173401)  1,2,4-Benzenetriol  ReagentPlus®, 99%

  • 533-73-3

  • 173401-5G

  • 2,604.42CNY

  • Detail
  • Vetec

  • (V900677)  1,2,4-Benzenetriol  Vetec reagent grade, 98%

  • 533-73-3

  • V900677-1G

  • 62.01CNY

  • Detail
  • Vetec

  • (V900677)  1,2,4-Benzenetriol  Vetec reagent grade, 98%

  • 533-73-3

  • V900677-5G

  • 162.63CNY

  • Detail

533-73-3Synthetic route

1,2,4-triacetoxybenzene
613-03-6

1,2,4-triacetoxybenzene

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 7h; Reagent/catalyst; Reflux;98%
With hydrogenchloride; methanol
With acetic acid
2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; for 0.833333h; Dakin Phenol Oxidation; Green chemistry;96%
With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h;85%
(4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one
1190844-34-8

(4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
In water at 170℃; for 2h; Inert atmosphere;93%
hydrogenchloride
7647-01-0

hydrogenchloride

triphenylantimony m-hydroxy-o-phenylenedioxide
187221-63-2

triphenylantimony m-hydroxy-o-phenylenedioxide

A

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

B

triphenylantimony dichloride
594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

Conditions
ConditionsYield
heating (3 h, water bath); soln. pouring into Petri dish, solid extraction by benzene;A 78%
B 86%
trans-3,5-dimethoxy-4-hydroxycinnamic acid
530-59-6

trans-3,5-dimethoxy-4-hydroxycinnamic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere;57%
aesculetin
305-01-1

aesculetin

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Sealed tube; Inert atmosphere;56%
recorcinol
108-46-3

recorcinol

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature;42%
With 2,6-dichloroquinone-4-chloroimide; sodium acetate; acetic acid
With water for 0.166667h;
hydroquinone
123-31-9

hydroquinone

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With <(Ce2(p-tert-butylcalix(8)arene))(Me2SO)5>*2Me2SO; dihydrogen peroxide In acetonitrile for 5h; Ambient temperature;39%
With sodium hydroxide
With oxygen; iron(III) In water pH=2.0; Kinetics; hydroxylation; Electrochemical reaction;
With titanium(IV) oxide In water at 30℃; Mechanism; Time; UV-irradiation;
Multi-step reaction with 3 steps
1: iodine; dihydrogen peroxide / water; sulfuric acid / 30 - 50 °C
2: sulfuric acid / 0.5 h / 25 - 50 °C
3: hydrogenchloride; water / methanol / 7 h / Reflux
View Scheme
2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one
78963-40-3

2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With phosphoric acid In water at 125℃; for 12h;39%
In water at 170℃; for 2h; Product distribution / selectivity; Inert atmosphere; Autoclave;95 %Chromat.
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

A

hydroxyquinone
2474-72-8

hydroxyquinone

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With air; methylene blue In methanol for 12h; Product distribution; Mechanism; Irradiation;A 15%
B 35%
4-hydroxysalicylic acid
89-86-1

4-hydroxysalicylic acid

A

hydroxyquinone
2474-72-8

hydroxyquinone

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With air; methylene blue In methanol for 12h; Product distribution; Mechanism; Irradiation;A 15%
B 35%
4,4-bis(ethylthio)-1,3-cyclohexanedione
112473-07-1

4,4-bis(ethylthio)-1,3-cyclohexanedione

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With mercury dichloride In methanol; water for 5h; Ambient temperature;32%
With acetic acid; mercury dichloride 1.) aqueous MeOH, r.t., 2.) reflux, 1 h; Yield given. Multistep reaction;
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

furfural
98-01-1

furfural

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

C

levulinic acid
123-76-2

levulinic acid

D

hydroquinone
123-31-9

hydroquinone

Conditions
ConditionsYield
In water at 330℃; under 210017 Torr; for 0.075h; Further byproducts given. Yields of byproduct given;A n/a
B 25%
C n/a
D n/a
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

furfural
98-01-1

furfural

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

C

levulinic acid
123-76-2

levulinic acid

D

hydroquinone
123-31-9

hydroquinone

E

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
In water at 330℃; under 210017 Torr; for 0.075h; other temperatures, other reaction times, other educt;A n/a
B 25%
C n/a
D n/a
E n/a
2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one
78963-40-3

2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one

A

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

B

benzene-1,2-diol
120-80-9

benzene-1,2-diol

Conditions
ConditionsYield
With zinc In acetic acid Product distribution; Further Variations:; Reagents; Temperatures; reductiv dehydration; reflux;A n/a
B 18%
D-fructose
7660-25-5

D-fructose

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
In water at 330℃; for 0.0513889h;9%
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

pyridine hydrochloride
628-13-7

pyridine hydrochloride

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
at 200 - 220℃;
1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With pyridine hydrochloride at 200 - 220℃;
2,4,5-trihydroxybenzoic acid
610-90-2

2,4,5-trihydroxybenzoic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
at 220℃;
p-benzoquinone
106-51-4

p-benzoquinone

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
ueber mehrere Stufen;
Multi-step reaction with 2 steps
1: sulfuric acid / 0.5 h / 25 - 50 °C
2: hydrogenchloride; water / methanol / 7 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; acetic acid / 40 - 50 °C
2: hydrogenchloride; water / methanol / 7 h / Reflux
View Scheme
3,4-dihydroxybenzaldehyde
139-85-5

3,4-dihydroxybenzaldehyde

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

1,2,4-Tris-(bis-trifluormethyl-aminooxy)-benzol
10545-14-9

1,2,4-Tris-(bis-trifluormethyl-aminooxy)-benzol

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With potassium hydroxide
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

furfural
98-01-1

furfural

B

5-Methylfurfural
620-02-0

5-Methylfurfural

C

5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

D

hydroxyquinone
2474-72-8

hydroxyquinone

E

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

F

levulinic acid
123-76-2

levulinic acid

Conditions
ConditionsYield
With water at 126.9℃; under 206266 Torr; Product distribution; Kinetics; Thermodynamic data; Ea, various water densities;
protonated cycloheptaamylose

protonated cycloheptaamylose

A

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

C

acetic acid
64-19-7

acetic acid

D

Glycolaldehyde
141-46-8

Glycolaldehyde

E

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

F

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With sodium chloride at 300℃; under 2 Torr; for 1h; Product distribution; other temperatures, other reaction times, or without 1percent aq. NaCl;A 1.1 % Chromat.
B n/a
C 3.7 % Spectr.
D 12.8 % Spectr.
E 1.6 % Spectr.
F 0.4 % Chromat.
4-chloro-phenol
106-48-9

4-chloro-phenol

A

4-chloro-1,2-benzenediol
2138-22-9

4-chloro-1,2-benzenediol

B

hydroxyquinone
2474-72-8

hydroxyquinone

C

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

D

hydroquinone
123-31-9

hydroquinone

E

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
ConditionsYield
With oxygen In water Product distribution; Irradiation;
benzene
71-43-2

benzene

A

[18O]phenol
1739-18-0

[18O]phenol

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

C

hydroquinone
123-31-9

hydroquinone

D

p-benzoquinone
106-51-4

p-benzoquinone

E

phenol
108-95-2

phenol

Conditions
ConditionsYield
With dioxygen-(16)O; 4-pentafluorophenyl perfluoro biphenyl; 18O-labeled water In acetonitrile; benzene Product distribution; Mechanism; Irradiation; ratio of C6H518OH to C6H5OH;
phenol
108-95-2

phenol

A

hydroxyquinone
2474-72-8

hydroxyquinone

B

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

C

benzene-1,2-diol
120-80-9

benzene-1,2-diol

D

hydroquinone
123-31-9

hydroquinone

E

p-benzoquinone
106-51-4

p-benzoquinone

F

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With oxygen; titanium(IV) oxide In water at 25℃; Product distribution; Quantum yield; Mechanism; Irradiation; various wavelengths, other catalysts;
1,2,4-Tris-(prop-1-enyloxy)-benzol
29873-12-9

1,2,4-Tris-(prop-1-enyloxy)-benzol

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Conditions
ConditionsYield
With hydrogenchloride
recorcinol
108-46-3

recorcinol

A

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

B

4-nitroso-1,3-benzenediol
698-31-7

4-nitroso-1,3-benzenediol

C

4-nitroresorcinol
3163-07-3

4-nitroresorcinol

D

2-hydroxyresorcinol
87-66-1

2-hydroxyresorcinol

Conditions
ConditionsYield
With potassium nitrate In water pH=5.7; Quantum yield; Kinetics; Further Variations:; Reagents; pH-values; wavelength; phototransformation; Irradiation;
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

dimethyl sulfate
77-78-1

dimethyl sulfate

1,2,4-trimethoxy-benzene
135-77-3

1,2,4-trimethoxy-benzene

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h;99%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;96%
With sodium hydroxide
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

1,2,4-tris(p-methoxybenzyloxy)benzene
1229578-67-9

1,2,4-tris(p-methoxybenzyloxy)benzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 18.3333h;97.1%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 18h; Cooling with ice;97.1%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

6,7-dihydroxy-4-methylcoumarin
529-84-0

6,7-dihydroxy-4-methylcoumarin

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 0.5h; Pechmann condensation; Microwave irradiation; regioselective reaction;97%
With zirconium(IV) chloride In toluene at 80℃; Pechmann Condensation; Inert atmosphere;95%
With phosphoric acid at 60℃;90%
methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

3,3,3-Trifluoro-2-hydroxy-2-(2,4,5-trihydroxy-phenyl)-propionic acid methyl ester
115167-56-1

3,3,3-Trifluoro-2-hydroxy-2-(2,4,5-trihydroxy-phenyl)-propionic acid methyl ester

Conditions
ConditionsYield
In benzene at 80℃; for 1h;95%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

tert-butyl[(4,4-dimethoxycyclohexyl)oxy]dimethylsilane
124414-01-3

tert-butyl[(4,4-dimethoxycyclohexyl)oxy]dimethylsilane

4′-[(tert-butyldimethylsilyl)oxy]spiro[benzo[d][1,3]dioxole-2,1′-cyclohexan]-5-ol

4′-[(tert-butyldimethylsilyl)oxy]spiro[benzo[d][1,3]dioxole-2,1′-cyclohexan]-5-ol

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In toluene Inert atmosphere; Schlenk technique; Reflux;95%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

2-(2'-benzothiazolyl)acetate

2-(2'-benzothiazolyl)acetate

C16H9NO4S

C16H9NO4S

Conditions
ConditionsYield
With piperidine In methanol for 5h; Reflux;95%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

ethyl 2-oxocyclohexane carboxylate
1655-07-8

ethyl 2-oxocyclohexane carboxylate

2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one

2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one

Conditions
ConditionsYield
With zirconium(IV) chloride In toluene at 80℃; Pechmann Condensation; Inert atmosphere;92%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-methyl-5,7-dihydroxycoumarin
2107-76-8

4-methyl-5,7-dihydroxycoumarin

Conditions
ConditionsYield
With nanosilica molybdic acid 2 In neat (no solvent) at 80℃; for 0.333333h; Pechmann Condensation; Green chemistry;91%
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

6,7-dihydroxy-4,4-dimethylhydrocoumarin

6,7-dihydroxy-4,4-dimethylhydrocoumarin

Conditions
ConditionsYield
86%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

phenyl propargyl ketone
3623-15-2

phenyl propargyl ketone

6,7-dihydroxy-2-phenylbenzopyrylium hexafluorophosphate

6,7-dihydroxy-2-phenylbenzopyrylium hexafluorophosphate

Conditions
ConditionsYield
With hexafluorophosphoric acid In acetic acid at 20℃; for 48h;86%
1,2,4,5-tetrachloro-3,6-dimethyl-benzene
877-10-1

1,2,4,5-tetrachloro-3,6-dimethyl-benzene

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

2-Ethoxy-5-hydroxy-2-methyl-1,3-dioxolane

2-Ethoxy-5-hydroxy-2-methyl-1,3-dioxolane

Conditions
ConditionsYield
86%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

2-chloro-5-(dichlorophosphanyloxy)-1,3,2-benzodioxaphosphole
1610473-86-3

2-chloro-5-(dichlorophosphanyloxy)-1,3,2-benzodioxaphosphole

Conditions
ConditionsYield
With phosphorus trichloride85%
With phosphorus trichloride In neat (no solvent) Inert atmosphere;85%
With phosphorus trichloride
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

α-bromoacetophenone
70-11-1

α-bromoacetophenone

C30H24O6
1320354-56-0

C30H24O6

Conditions
ConditionsYield
With triethylamine at 20℃;84.11%
1-decanoic acid
334-48-5

1-decanoic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

3,4-dihydroxyphenyl n-decanoate

3,4-dihydroxyphenyl n-decanoate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 20h;84%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0℃; for 20h;
ethyl (2-chloroaceto)acetate
638-07-3

ethyl (2-chloroaceto)acetate

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

4-chloromethyl-5,7-dihydroxy-chromen-2-one
809234-33-1

4-chloromethyl-5,7-dihydroxy-chromen-2-one

Conditions
ConditionsYield
With nanosilica molybdic acid 2 In neat (no solvent) at 80℃; for 0.333333h; Pechmann Condensation; Green chemistry;84%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

(2,5-bis-tert-butoxycarbonylmethoxy-phenoxy)-acetic acid tert-butyl ester

(2,5-bis-tert-butoxycarbonylmethoxy-phenoxy)-acetic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 1h; Williamson reaction; Heating;81%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

[1,1′-biphenyl]-2,2′,4,4′,5,5′-hexaol
76625-61-1

[1,1′-biphenyl]-2,2′,4,4′,5,5′-hexaol

Conditions
ConditionsYield
With oxygen; Y2(Sn0.7Ce0.3)2O7 In water at 100℃; for 12h; Reagent/catalyst; Temperature;80.2%
With air In water for 20h; Time; Solvent; Reflux;
With oxygen In water at 100℃; for 72h; Green chemistry;94.4 %Chromat.
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

2,2-Dimethyl-5-hydroxybenzo[1,3]dioxole
73447-99-1

2,2-Dimethyl-5-hydroxybenzo[1,3]dioxole

Conditions
ConditionsYield
Stage #1: 1,2,4-Trihydroxybenzene With pyridinium p-toluenesulfonate In toluene Reflux;
Stage #2: 2,2-dimethoxy-propane In toluene for 1.83333h;
80%
With pyridinium p-toluenesulfonate In toluene for 1.83333h; Reflux;57%
Stage #1: 1,2,4-Trihydroxybenzene; 2,2-dimethoxy-propane With toluene-4-sulfonic acid In toluene at 130℃; for 1.5h;
Stage #2: With sodium methylate In methanol; toluene at 20℃;
28.9%
With pyridinium p-toluenesulfonate In toluene at 110℃; for 2h;
With pyridinium p-toluenesulfonate In ethyl acetate at 85℃; Inert atmosphere;
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

1-(2,4,5-trihydroxyphenyl)-2-(4'-methoxyphenyl)ethanone
76095-38-0

1-(2,4,5-trihydroxyphenyl)-2-(4'-methoxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 1,2,4-Trihydroxybenzene; p-methoxybenzylnitrile With hydrogenchloride; zinc(II) chloride In diethyl ether at 0 - 20℃;
Stage #2: With water In methanol Reflux;
79.6%
With hydrogenchloride; zinc(II) chloride at 0℃;
3-Methylbutenoic acid
541-47-9

3-Methylbutenoic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

2,2-Dimethyl-6,7-dihydroxy-4-chromanone
76348-95-3

2,2-Dimethyl-6,7-dihydroxy-4-chromanone

Conditions
ConditionsYield
With zinc(II) chloride; trichlorophosphate at 50℃; for 5h;79%
dichloro(hydrotris(3,5-dimethyl-1-pyrazolyl)borato)oxomolybdenum

dichloro(hydrotris(3,5-dimethyl-1-pyrazolyl)borato)oxomolybdenum

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

(hydrotris(3,5-dimethyl-1-pyrazolyl)borato)oxomolybdenum(V)(O2C6H3-4-OH)

(hydrotris(3,5-dimethyl-1-pyrazolyl)borato)oxomolybdenum(V)(O2C6H3-4-OH)

Conditions
ConditionsYield
With triethylamine In toluene (N2); addn. of toluene and triethyl amine (excess) to a mixture of Mo-complex and 1,2,4-benzenetriol; heating to 80°C with vigorous stirring; helding there for 1 h; evapn. to dryness (vac.); adsorption chromy. on silica gel; recrystn. from dichloromethane/hexane;79%
3,4-dimethoxycinnamic acid
2316-26-9

3,4-dimethoxycinnamic acid

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

6,8-dihydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrocoumarin

6,8-dihydroxy-4-(3,4-dimethoxyphenyl)-3,4-dihydrocoumarin

Conditions
ConditionsYield
With sulfated montmorillonite K-10 In nitrobenzene at 100℃;79%
With montmorillonite K-10 at 100℃;
Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; diastereoselective reaction;76%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one
7758-73-8

5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one

Conditions
ConditionsYield
With nanosilica molybdic acid 2 In neat (no solvent) at 80℃; for 0.333333h; Pechmann Condensation; Green chemistry;76%
1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline
95377-69-8

4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline

4-{[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]diazenyl}benzene-1,3-diol

4-{[4-(1H-imidazo[4,5-b]pyridin-2-yl)phenyl]diazenyl}benzene-1,3-diol

Conditions
ConditionsYield
Stage #1: 4-(1H-imidazo[4,5-b]pyridin-2-yl)aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: 1,2,4-Trihydroxybenzene With sodium hydroxide In water at 0 - 5℃; for 2h;
76%
4-cyanomethylphenol
14191-95-8

4-cyanomethylphenol

1,2,4-Trihydroxybenzene
533-73-3

1,2,4-Trihydroxybenzene

1-(2,4,5-trihydroxyphenyl)-2-(4'-hydroxyphenyl)ethanone
76095-37-9

1-(2,4,5-trihydroxyphenyl)-2-(4'-hydroxyphenyl)ethanone

Conditions
ConditionsYield
Stage #1: 4-cyanomethylphenol; 1,2,4-Trihydroxybenzene With hydrogenchloride; zinc(II) chloride In diethyl ether at 0 - 20℃;
Stage #2: With water In methanol Reflux;
75.4%
With hydrogenchloride; zinc(II) chloride at 0℃;

533-73-3Relevant articles and documents

Titanosilicate molecular sieve for size-screening photocatalytic conversion

Shiraishi, Yasuhiro,Saito, Naoya,Hirai, Takayuki

, p. 8304 - 8306 (2005)

Titanosilicate molecular sieves, when activated by ultraviolet light irradiation in water in the presence of molecular oxygen, catalyze a conversion of molecules having a size close to the pore of the catalysts but are inactive for molecules having much larger or smaller size. This unprecedented size-screening photocatalytic activity is triggered by a combination of H2O-induced shortened lifetime of active species (charge-transfer excited state of tetrahedrally coordinated titanium oxide) and restricted diffusion of a molecule inside the pore. This catalytic property demonstrates a potential utility of the catalyst for selective transformation of molecules that is associated with a size reduction of molecules, so-labeled molecular shave transformation. Copyright

Enhanced nonradical catalytic oxidation by encapsulating cobalt into nitrogen doped graphene: highlight on interfacial interactions

Yu, Xiaoyong,Wang, Lijing,Wang, Xin,Liu, Hongzhi,Wang, Ziyuan,Huang, Yixuan,Shan, Guoqiang,Wang, Weichao,Zhu, Lingyan

supporting information, p. 7198 - 7207 (2021/03/29)

Supported metal catalysts are widely used for heterogeneous catalytic processes (e.g., Fenton-like reaction), but the mechanisms of interfacial processes are still ambiguous. Herein, unique nanocarbon based catalysts with Co nanoparticles encapsulated in

Antagonistic activity of hydroxycoumarin-based antioxidants as possible singlet oxygen precursor photosensitizers

Guerrero, Tomás,Vázquez-Ortega, Fernanda,Lagunes, Irene,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo,Medina, Manuel E.,Trigos, ángel

, (2021/05/10)

Coumarins are phenolic-type compounds with efficient antioxidant activity due to their ability to scavenge reactive oxygen species. Nevertheless, their ability to behave as photosensitizers capable of generating reactive oxygen species, such as singlet oxygen, has been less studied. In this work, the photosensitizing ability of seven hydroxycoumarins was evaluated through the photooxidation of ergosterol by quantifying the conversion of ergosterol into ergosterol peroxide. In our experimental conditions, we found that almost every tested antioxidant coumarin promotes the peroxidation of ergosterol. The results suggest that the hydroxycoumarins exhibit potential photosensitizing activity by promoting singlet oxygen generation by a Type II photochemical mechanism. Density functional theory (DFT) calculations were also performed to obtain further insight into the chemical reactivity of tested compounds; the observed tendency in the group of antioxidant coumarins to promote the reaction was their hardness due to the principle of maximum hardness. To evaluate our conclusion, we performed the reaction using a highly polarizable coumarin as a photosensitizer, which resulted in an increased photosensitizing capacity supported with DFT calculations, which reinforces our analysis. Finally, we found that hydroxycoumarins can be potentially pro-oxidants since some of them can act as photosensitizers and generate singlet oxygen in the presence of UV–Vis light, a characteristic that must be considered when these compounds are used as antioxidants.

Synthesis of renewable C-C cyclic compounds and high-density biofuels using 5-hydromethylfurfural as a reactant

Cai, Taimei,Deng, Qiang,Deng, Shuguang,Gao, Rui,Peng, Hailong,Wang, Jun,Zeng, Zheling,Zhong, Jin,Zou, Ji-Jun

, p. 2468 - 2473 (2020/05/14)

The major challenge in the synthesis of high-density biofuels is to identify the bio-based source for C-C cyclic compounds and C-C coupling reactions with a suitable selectivity. Herein, we selectively synthesize 1,2,4-benzenetriol (BTO) with a yield of 51.4% from cellulose-derived 5-hydromethylfurfural via a ring-rearrangement reaction. The cellulose-derived route is a more meaningful route for the C-C cyclic compounds compared to the traditional hemicellulose- and lignin-derived routes. Furthermore, BTO is very easily dimerized via a C-C oxidative coupling reaction, showing a yield of 94.4% and selectivity of nearly 100% under environmentally friendly reaction conditions. After hydrodeoxygenation, bicyclohexane is obtained with a yield of 87.4%. This work not only provides a promising route to produce C-C cyclic fine compounds based on a cellulose-derived route, but also shows a highly efficient synthesis route for high-density biofuels via the C-C oxidative coupling reaction.

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